CONFIDENTIAL SEARCH
CHIEF PILOT
Lead Safe, Compliant and High-Performing Fixed-Wing Operations | Western Canada
A confidential, family-owned aviation operator in Western Canada is seeking an accomplished Chief Pilot to provide operational leadership, develop pilot capability, and uphold the highest standards of safety, regulatory compliance and professionalism. The organization offers a genuine team environment and values sustainable operations, flexibility and work-life balance.
The Opportunity
This is a key leadership position within flight operations, reporting to the Director of Flight Operations. The Chief Pilot will oversee the safe and efficient operation of company fixed-wing aircraft and lead the pilot group across recruitment, training, qualification, performance and day-to-day operational readiness.
The successful candidate will be both a credible aviation professional and an engaged people leader — someone who can translate regulatory requirements into clear standards, coach and mentor pilots at different stages of their careers, and build a culture of trust, accountability, learning and continuous improvement.
What You Will Lead
- Provide visible, hands-on leadership and supervision to flight crews, ensuring company fixed-wing aircraft are operated safely, efficiently and in accordance with applicable regulations, manuals and policies.
- Establish, maintain and continuously improve approved flight crew ground and flight training programs.
- Develop and maintain standard operating procedures, flight operations manuals, operational directives and notices.
- Implement initial and recurrent training and periodic checks, ensuring each flight crew member is competent, qualified on type and meets applicable Pilot Proficiency Check standards.
- Ensure flight crews are trained and assessed in emergency procedures, emergency evacuation, life-saving equipment and other required safety practices.
- Maintain accurate pilot records, qualification files, examinations and a current operational information library in accordance with company and regulatory requirements.
- Lead pilot recruitment, onboarding, evaluation and performance management; provide regular coaching, constructive feedback and career mentorship; and, where required, manage corrective or disciplinary processes fairly and consistently.
- Work closely with operations, maintenance, safety, compliance and human resources as one integrated team to support crew readiness, aircraft availability and effective workforce planning.
- Support incident and occurrence investigations, complete corrective action plans, and process crew, accident and incident reports.
- Monitor regulatory developments, industry trends and emerging technology to keep flight operations current and effective.
Reporting and Operational Oversight
- Prepare and present flight operations performance reports and recommendations to senior leadership.
- Analyze operational data and trends to identify risks, efficiencies and opportunities for improvement.
- Monitor and report on pilot performance, training, qualifications and staffing readiness.
- Provide accurate pilot-hours information to support compensation administration and workforce planning.
- Act on responsibilities delegated by the Director of Flight Operations and ensure qualified coverage is appointed during absences, in accordance with applicable requirements.
What You Bring
- A valid Transport Canada Airline Transport Pilot Licence or Commercial Pilot Licence for fixed-wing aircraft, together with a valid Instrument Rating and demonstrated IFR experience.
- At least 500 hours of flight time.
- Qualification, or the ability to qualify, under the operator's flight training program to act as pilot-in-command on at least one aircraft type operated by the organization.
- Strong working knowledge of the Canadian Aviation Regulations, Commercial Air Service Standards and safety management principles.
- Demonstrated experience leading pilots or flight operations, including training, performance oversight and operational decision-making, with a track record of setting clear expectations and following through on commitments.
- Sound judgment, analytical thinking and the ability to make clear, safety-focused decisions in dynamic operating environments.
- Strong communication, planning and relationship-building skills, with the ability to listen, build trust, navigate difficult conversations and work effectively across departments and with regulators and external stakeholders.
- A practical, approachable and adaptable leadership style, with a genuine commitment to mentoring others, sharing knowledge, developing future leaders and recognizing the strengths of each team member.
Additional Requirements
This is a safety-sensitive position within a federally regulated aviation environment. Employment is subject to all applicable fit-for-duty, licensing, medical, training, security and regulatory requirements. These may include pre-employment and post-incident drug and alcohol testing, as permitted or required, as well as role-specific operational and customer-site training. A valid driver's licence and the ability to complete required aviation, safety and equipment training may also be required.
Why You'll Enjoy Working Here
- Visible leadership impact: Influence the standards, systems and decisions that shape safe, effective flight operations.
- Meaningful people leadership: Develop and mentor a skilled pilot group, build future leaders and strengthen operational capability.
- A great team culture: Join a close-knit, family-owned business where collaboration, mutual support and individual contributions are genuinely valued.
- Work-life balance: Work within an organization that values planning, communication, flexibility and a practical, sustainable approach to work.
- A unique aviation environment: Lead within a dynamic operation and work closely with pilots, maintenance, safety and operational teams.
Apply in Confidence
Qualified candidates are invited to submit a resume outlining their flight experience, licences, aircraft qualifications and leadership background. All applications and inquiries will be handled confidentially.
We thank all applicants for their interest. Only candidates selected for further consideration will be contacted.
Pay: $40.00-$43.00 per hour
Benefits:
Work Location: In person
